Pyridine → HCID 89797896, compound

HRID 922329Notes

Reaction equation

HRID 922329 reaction equation
[OH:1][CH:2]([CH:7]([OH:34])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23]/[C:24](=[N:31]\[O:32][CH3:33])/[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].N1C=CC=C[CH:36]=1.Cl[C:42](Cl)([O:44]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH3:33][O:32]/[N:31]=[C:24](/[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)\[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH:7]3[O:34][C:42](=[O:44])[O:1][CH:2]3[C:3]([O:5][CH2:6][CH3:36])=[O:4])=[CH:9][CH:10]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 87106533HCID 87106533, compound

Product 1

HCID 89797896HCID 89797896, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of methyl 2,3-dihydroxy-3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}propanoate (1.3 g, 2.8 mmol) in dichloromethane (20 mL) was added pyridine (1.4 g, 17.7 mmol) at −78° C. followed by solution of triphosgene (0.44 g, 15 mmol) in dichloromethane, and gradually warmed to RT then stirred at RT for 4 h. RM quenched with 1N HCl and extracted with dichloromethane. Organic layer was washed with water, NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated to colourless oil which was purified by column (60-120 silica) using 20% ethyl acetate in pet ether to get the titled compound as colourless oil. (0.8 g, Yield: 58%) 1H NMR (300 MHz, CDCl3): δ 7.62-7.64 (m, 2H), 7.34-7.45 (m, 8H), 7.06-7.09 (d, 2H), 6.91-6.94 (d, 2H), 5.88-5.91 (d, 1H), 5.41-5.44 (d, 1H), 5.23 (s, 2H), 5.04 (s, 2H), 3.99 (s, 3H), 3.76 (s, 3H).

Workup

  1. customRM quenched with 1N HCl
  2. extractionextracted with dichloromethane
  3. washOrganic layer was washed with water, NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated to colourless oil which
  6. customwas purified by column (60-120 silica)

Sources & evidence

ORD record
ord-b4804bc24cbe44aa99c6441b4f0c22a4
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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